


Little Red Riding Stiles

by MasculineSuccubus (PJStories)



Category: Teen Wolf (TV)
Genre: Alpha Derek, Alpha Derek Hale, Alpha Mate Stiles Stilinski, Alpha Scott McCall (Teen Wolf), Alpha/Beta/Omega Dynamics, Alternate Universe - Fairy Tale, Alternate Universe - Little Red Riding Hood Fusion, Anal Fingering, Anal Sex, Bottom Stiles Stilinski, Boypussy, Boypussy Stiles Stilinski, Cock Slut, Cock Slut Stiles Stilinski, Consensual Underage Sex, Creeper Peter Hale, Cunnilingus, Derek Hale as the Big Bad Wolf, Derek Hale is a Softie, Everyone Loves Stiles Stilinski, Fairy Tale Elements, Fairy Tale Parody, Fairy Tale Retellings, Fairy Tale Style, First Time, First Time Bottoming, Fivesome - M/M/M/M/M, Fluff and Smut, Funny, Gay Porn Hard, Horny Stiles Stilinski, Jackson Whittemore is Part of the Pack, Knotting, Loss of Virginity, M/M, Mates Derek Hale/Stiles Stilinski, Mating, Mating Bites, Mating Bond, Mating Cycles/In Heat, Mating Rituals, Mpreg, Multi, My First Work in This Fandom, Omega Stiles Stilinski, Oral Sex, Other Additional Tags to Be Added, Pack Bonding, Pack Dynamics, Pack Mom, Pack Mom Stiles Stilinski, Penis In Vagina Sex, Polyamorous Pack, Polyandry, Porn, Porn Parody, Porn With Plot, Possessive Derek, Pregnancy, Pregnancy Kink, Pregnant Stiles Stilinski, Protective Derek, Protective Pack, Protective Scott, Protective Scott McCall (Teen Wolf), Scared Stiles Stilinski, Scott McCall as the Woodsman, Shameless Smut, Slut Stiles Stilinski, Smut, Squirting, Stiles Stilinski Gives Oral Sex, Stiles Stilinski Has a Vagina, Stiles Stilinski as Little Red Riding Hood, Stiles Stilinski in Heat, Stiles Stilinski is a Squirter, Teen Pregnancy, The Hale Pack - Freeform, Top Derek, Top Derek Hale/Bottom Stiles Stilinski, Top Isaac Lahey, Top Jackson Whittemore, Top Peter Hale, Top Scott McCall (Teen Wolf), Top Vernon Boyd, Vaginal Fingering, Vaginal Sex, Virgin Stiles Stilinski, Virginity
Language: English
Status: In-Progress
Published: 2021-02-17
Updated: 2021-02-17
Packaged: 2021-03-12 19:22:34
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,211
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29514573
Author URL: https://archiveofourown.org/users/PJStories/pseuds/MasculineSuccubus
Summary: "You're supposed to say, 'What a mighty strong tongue you have!'" "Seriously? Are we really doing this? My grandmother is a human woman!""All the better to eat your pussy with, my dear."Stiles Stilinski lives a simple life as the son of the Sherriff of the quiet town of Fairy Beacon Hills, which may or may not have a werewolf problem. Virginal and awkward, but hilarious and sexy as fuck, if he doesn't say so himself, Stiles is content to spend his time with his best friend Lydia, chasing away the spiders that gave her PTSD, and occasionally giving himself carpal tunnel jilling off to his crush, the hot woodsman.One day, despite his protestations, his father sends him off to tend to his ailing grandmother at her cabin in the woods, ordering him to keep to the path and to NEVER take off his protective amulet, but Stiles is seventeen and tired of following the Sherriff's rules. He's ready to make his own path, and if that means getting eaten out--or alive!--by werewolves, who probably don't even exist, so be it.It's time for the boy in the red riding hood to learn that the best things in life lie off the beaten trail, and sometimes, sexy, naked men wandering through the woods give the best head.
Relationships: Derek Hale/Stiles Stilinski, Isaac Lahey/Stiles Stilinski, Peter Hale/Stiles Stilinski, Scott McCall/Stiles Stilinski, Stiles Stilinski/Everyone, Stiles Stilinski/Jackson Whittemore, Stiles Stilinski/The Pack, Vernon Boyd/Stiles Stilinski
Comments: 5
Kudos: 119





	Little Red Riding Stiles

**Author's Note:**

> This work is an original Teen Wolf erotic fan-fiction. All rights, other than those pertaining to the Teen Wolf franchise, are owned by me. Do not copy or share this work without my consent.
> 
> This is a comedic, smutty take on a popular fairy tale, set in the Teen Wolf multiverse, complete with polyamorous werewolves, boys in red riding hoods looking to give up their maidenhoods, and a fivesome-turned-sixsome with so much bodily fluids that a certain old woman will probably need to live in her friend's shoe condo for the foreseeable future.
> 
> Trigger warnings: sexual innuendo? (seriously, this first chapter--and the story in general!--is pretty harmless. Smutty as Hell, and starring a seventeen-year-old Stiles, but otherwise everything is perfectly consensual and fun and loving for all parties involved. It's a feel-good break from the darker, melodramatic shit I usually post.) MIND THE TAGS!
> 
> I had originally planned on writing this as a one and done long-fic, but thought that breaking it up into smaller chapters and then extending into multiple fairytales after the first would be more fun and easier on me. See my notes at the end for posting schedule and updates on this channel. As always, kudos, comment, subscribe! 
> 
> Enjoy! :)

Stiles and his father were standing in the kitchen of their two story cottage on the edge of town, discussing a change of plans that had the only son of the sheriff of Fairy Beacon Hills cursing his luck. 

“Dad, do I have to?” Stiles whined. “Grandma lives so far away, and besides I was gonna go see Lydia today. Her mom gives her all the worst parts of the cheese making process, and we were gonna go huck em at spiders. She can’t do it alone because of her PTSD from that one time that giant black widow fell onto her tuffet. Deaton says it should be therapeutic, and I know he’s only a horse-doctor, but ever since the surgeon bled himself to death trying to cure his penis pox—“

“Enough, Stiles!” the sheriff shouted, spinning around from the basket he was filling up with foodstuffs. “I don’t want to hear another word about Miss Muffet or her tuffet. Got it?”

Stiles groaned, kicking the bare wood floor with his boots. “But daaaadd!”

“No buts, mister. Now you are going to go to your grandma’s today, and you aren’t coming back until the end of the week.”

“What!? The end of the week! Dad!”

“No buts!”

“Well technically I didn’t say a ‘but’ there.”

“Stop talking!” the sheriff shouted, going red in the cheeks. “God of all magic, can you go five minutes without interrupting me?”

Five minutes would be a long time, Stiles thought, but he could also see that his dad was getting apoplectic, and the last thing he wanted was for the old man to have a stroke or a heart attack—why else did he keep trying and failing to put the sheriff on a healthy diet?!—so for once, though it panged him to do so, he shut his trap, letting his father at least finish his instructions before listing all of his complaints. 

“Thank you,” Sheriff Stilinski said. “Now where was I? Right. Your grandma. Now as you know, your grandma’s getting on in years…”

 _As grandmas tend to do_. Stiles thought, but kept it to himself. 

“She’s not long for this life. I just received word this morning that she’s taken ill, and before you say anything, it’s not the plague. I don’t think it’s even anything contagious. The woodsman wasn’t very specific on that.”

 _The woodsman?!_ Stiles jumped, unable to contain his words about someone with whom he was so twitterpated. Maybe going to his grandma’s wouldn’t be so bad after all. 

“Wait, the hot woodsman?” he said. “The hot woodsman was here, and you didn’t tell me!”

“What?” his dad said.

“He’s about yea high. Full head of dark hair. Tan. Smoldering eyes. Pronounced chin that’s turned a bit to the left. Broad shoulders. Glistening, rock hard pecs and washboard abs. Thick, beefy arms when he swung that heavy axe into those logs, splitting them in half.”

Stiles could feel the warm slick beginning to drip out of his mossy cavern as he remembered all of the dreams he’d had where he’d been the one getting split in half. 

“Stiles!”

Stiles realized he’d been biting his lip. Orgasm eyed and practically panting, Stiles pulled himself out of his horny headspace, averting the sheriff’s gaze and blushing a deep scarlet. 

“I think his name was Mike, or something. There was definitely an M in there, somewhere. Or did his name start with an S? Skip or Scotch or Studly McStuderson?”

“For God’s sake, Stiles!”

“What? I didn’t name him. You should question his mom about why she’d give her son such an erotic name. Maybe he was named after his father?”

Wouldn’t that be the dream double-team. Studly junior and Studly senior going to town on his great divide. Putting in the ingredients for a Studly the third. Yeah, Stiles would name their son Studly. He wasn’t going to come in the way of a dynasty. But he could see that his dad was fast on his way towards another apoplexy, so he stored that scenario for later. 

“Anyway, grandma’s sick?”

The sheriff let out a long, beleaguered sigh. “Yes. Your grandma’s sick. And I want you to go spend some time with her and nurse her back to health. Or if it’s looking like that’s not going to happen, at least be there for her when she dies. You can ask the woodsman to help you bury her if need be, but no funny business!”

“DAAADD!”

Did his father really think he was going to have sex after burying his grandma? 

Well, actually, now that he thought about it he would be pretty sad and in need of comforting, and where better to look for it than in the arms of a hunky, trusted stranger who he’d ogled far too many times and for far too long when he’d last visited his grandma a couple of months ago.

Stiles didn’t think about that too much, though. He certainly didn’t want his grandma to die. Besides there were easier ways of seducing old Studly. Hopefully just with body language, as when he opened his mouth he tended to ramble through his unfiltered thoughts, which was enough to make anyone flaccid. It was as bad as tying a red flag around his neck—Avoid Stiles! He can’t shut up, and he’ll probably say something wildly inappropriate!

At least he was cute. Adorable even, he conjectured. Down right sexy with his perky buns, kissably plump lips, pasty, nay, fair skin—like the polished alabaster of an ancient idol!—thick, pullable, dark-brown hair, whiskey-colored irises, and long, elegant neck. Lean and muscular, though nothing compared to old Studly, with a noticeable thickness in all the right places, he still retained much of the softness of his youth, alongside a general hairlessness, which was the only feature he would have changed.

His father brought him back from his musings by dropping the heavy basket with a thud onto their flimsy, ancient dining room table. 

“I know you’re attracted to men, and I’ll support you no matter what, but it’s a dangerous world out there, and I just want you to be careful.” the sheriff said, reaching out to squeeze his son on the shoulder. 

“I am careful, dad.” Far more careful than he wanted to be. He was the oldest virgin he knew. Still, it was nice that the sheriff cared enough to worry. Didn’t stop his concern from being stifling. And it didn’t help his closeness with the old man that his worries would have vanished had Stiles been born with a dick and an interest in Lydia’s tuffet that went beyond comparing sizes. 

“It’s bad enough you were born with that mysterious, shadow-box theater down there.” Sheriff Stilinski circled his hand in the general direction of Stiles’ crotch, eyeing his son’s pelvis with a suspicious glare, as if he didn’t trust it not to break free from Stiles’ body and go on a killing spree throughout the town. 

Stiles groaned. “We’ve been over this dad. It’s called a vagina.”

“Quiet!” the sheriff hissed. “Do you want the neighbors to hear?”

Rolling his eyes, tired of his dad’s concern/terror about his pussy, Stiles pointed his finger towards the window. 

“Our nearest neighbors are half a mile that way. Do you really think they can eavesdrop on our conversation?”

Sheriff Stilinski closed the blinds, answering his son’s rhetorical question in the affirmative. 

“Just keep it down. Don’t tell anyone about it, and definitely don’t go showing it off. Who knows what they’ll do to you if someone should find out. They might throw you out to the werewolves…”

 _And now we’re back to werewolves_ , Stiles thought with a groan, his father’s favorite obsession.

“...and then how would I be able to protect you? Boys in your…” the sheriff stammered, trying to find the right word for something he obviously found deeply uncomfortable, “situation are like candy to those creatures. They’ll eat you alive!”

“Wouldn’t that be nice,” Stiles moped. 

“Stiles!”

“I was just kidding.”

The sheriff wasn’t laughing.

“You’ve heard what the Argents said about young boys like you. Omegas, I think, was the word they used.”

“Ugggh. Dad, how many times must we go through this? I’m seventeen, which, last time I checked, is hardly young. Most girls my age have already died in childbirth…”

“You know I hate that comment.”

“Secondly,” Stiles continued. “Omegas are not werewolf food. They’re more like werewolf queens.”

“Painted boy-whores,” the sheriff grumbled. 

“A noble profession,” said Stiles slyly.

“My foot! I—”

“And lastly,” Stiles interjected, “and most importantly, have the Argents ever, oh, I don’t know, _caught_ a werewolf? Have they ever even proved that they exist?”

The answer of course was no. Stiles knew it, the sheriff knew it, but his dad had bought into the town’s werewolf hysteria, melting all of his late mother’s silverware so that the Argent’s could forge protective amulets for them for a hefty fee. 

“... I mean, they haven’t brought one back to town...” the Sheriff fumbled, “but there have been plenty of tracks.”

“Right,” said Stiles, “and of course, there isn’t any other animal capable of making wolf prints… oh wait!”

“Don’t start with that again—“

“A wolf can make wolf prints.”

“These were different! They were larger than regular wolf prints.”

“By how much, exactly?”

“An inch,” the sheriff admitted, “which is still significant!”

“Oh cut the crap, dad,” said Stiles. “Just admit that werewolves aren’t real! They don’t exist.”

“Of course werewolves exist! And I’m not having this conversation with you again,” Sheriff Stilinski said, grabbing the basket and thrusting it into his son’s hands, taking Stiles by the shoulders and walking him towards the door. “There’s enough food in there to last you a week.”

“Hey!” Stiles griped, trying to ground his feet against the floor, but the sheriff just kept pushing forward until he had to walk or fall flat on his face. “I didn’t agree to this!”

“Are you wearing your amulet?” the sheriff asked nonplussed, steering his belligerent son towards the coat rack. 

“Yes, but—“

“Here, put on your cloak. It’s cold out.”

“It’s a riding hood! Cloaks are thicker. And I haven’t had my chance—”

Stiles tried to fidget, but the basket was heavy, and his dad’s hands never let him be for long, tying the red hood about his neck before turning him around and pushing him past the threshold of their open front door. 

“Send your grandma my love. Stay on the trail. And whatever you do, don’t take off your amulet!”

“Hey! I never—“

But the sheriff had slammed the door in his face. Soon after he heard the lock click and knew that there would be no reasoning with his old man. 

That didn’t make him any less angry about having his freedom taken away. Fuming, he thought about banging on the door, but that would only result in him injuring his fist. The door was made of heavy wood after all. If only there was some other way he could show his defiance. And then it came to him. The amulet!

He pulled with all his might on the leather cord around his neck, letting out an involuntary yelp at the pressure required to snap it. That was definitely going to leave a bruise. Still, if nothing else happened to his sensitive neck that day he’d be fine. 

The silver amulet weighed heavily in his palm. Covered in odd runes and crude pictures of werewolves, Stiles couldn’t help but admire the attention to detail. There wasn’t a spot on the surface left unmarked. If it hadn’t cost all of his mom’s dowry, he might have appreciated it as an ornament if nothing more. But now it just stood as a symbol of his father’s stubborn pigheadedness. Shifting the hefty basket—probably filled with nothing but sweets, cheese and dried meat since the sheriff had packed it, and, though Stiles had tried to convince him otherwise, he thought all vegetables were rabbit food—into the crook of his arm, he hucked the talisman at the door where it impacted the wood with a deafening dun. 

As the amulet hit the patch of dry dirt that served as their front stoop, Stiles felt a twinge of guilt. As much as he wanted to assert his independence, he knew that his father would panic if he found the amulet lying in the dirt. He’d probably run himself ragged chasing through the woods looking for what he thought would be his son’s dead body. That is if he didn’t have a heart attack first. Stiles couldn’t have that happen, but he also wasn’t about to put it back on in defeat. Instead, he kicked the amulet into a low, dense bush so that it was safely out of sight. 

Guilt and fear stymied, Stiles puffed out his chest, feeling powerful. He would still go to his grandma’s, mostly because he was truly concerned about her health and would gladly do whatever was needed to help her, but maybe he wouldn’t stick to the trail. And maybe, hopefully, God willing, if there was any goodness in this universe at all, he would get up to some funny business before the day was through.

**Author's Note:**

> Hi everyone! I hope you enjoyed this first chapter.
> 
> I post new content every Sunday and most Wednesdays, either new chapters on current stories or new stories I'm working on. 
> 
> I know that I was supposed to release a new chapter of Comfort and Shame today, but I couldn't finish it in time (its a long one!). Hopefully chapter 2 will be up by Sunday. Otherwise, Sunday will probably be my new Drarry fic (or one of the shit-ton other stories I've been working on), and chapter 2 of Comfort and Shame will be up next Wednesday. Chapter 4 of the Milker is ready to go, but I'm going to wait another couple of weeks before posting because I just posted chapter 3 and want to allow that one time to simmer. 
> 
> Subscribe to my author account to be updated whenever I post new content, or just subscribe to the individual stories if you would prefer.
> 
> Have an excellent rest of your day!


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